Navigating Difficult Conversations

May 26, 2019


With Millennials quickly moving into management, a generation more comfortable with texting than talking has overtaken the legal workplace. Yet, a one-on-one conversation with an internal or external client remains the fastest and most effective way to resolve conflicts, negotiate solutions, and improve performance.

Professional development experts in law firms and law schools must take the lead in helping legal professionals acquire this critical skill.

Why provide difficult-conversations training?

The ability to manage difficult conversations is an essential business skill that is critical to building relationships and serving clients. Too many lawyers avoid these conversations, usually because they worry that a colleague or client will react defensively to what needs to be said. Consider the following scenarios:

  • A new equity partner believed her authority had been challenged by a junior associate who questioned the aggressive tax strategy that the partner had developed. Initially, the new partner asked two senior members of the practice group to intervene. When those lawyers declined, the new partner settled on a two-step approach: 1) sit in her office and fume; and 2) avoid future interactions with the junior associate.
  • Several law firm associates complained that they now anticipate email “dumps” of major projects around 3:00 p.m. each Friday. One associate said he lives in a state of perpetual anger. Faced with managing the competing expectations of multiple partners, he hesitates to say: “Here’s what I’m currently working on. If I return this project to you by Tuesday, will that meet your needs?”
  • Some new associates avoid communication altogether. Contacts in multiple firms have told me about new associates who fail to tell anyone that they will not meet a deadline until it’s nearly too late. And I regularly hear about new lawyers who do not share their personal plans (a vacation, a long-weekend escape) until a managing lawyer says, “Tomorrow, I need you to….” After the junior replies, “But I have a nonrefundable airline ticket to …,” everyone leaves the exchange feeling frustrated and angry.

Lawyers require communication skills that will help them achieve desired business results while facilitating the important relationships that are critical to the success of any professional services organization. Difficult-conversations training meets that need.

What are the most important components of a difficult-conversations training module?

Every PD professional within the legal industry knows that lawyers love easy-to-use models and checklists. Douglas Stone, Bruce Patton and Sheila Heen, all of whom have been affiliated with Harvard Law School and/or the Harvard Negotiation Project, have created a model that anyone may use to navigate a conversation that feels difficult to them. Key components include:

1.  Before the conversation, self-reflect

  • Develop an understanding of your perception of a set of facts while recognizing that you can’t know another person’s intentions, perspectives or feelings unless he or she shares them with you;
  • Acknowledge your feelings regarding your perceptions without judgment and accept that anyone who participates in the conversation likely possesses equally intense feelings; and
  • Recognize that any difficult conversation will challenge your beliefs regarding whether you are competent or incompetent, good or bad, worthy of respect or not.

2.  Focus on problem-solving and moving forward

  • Avoid assigning blame for past facts;
  • Think like a mediator and search for a meaning that describes the particular conversation’s central issue in a way that rings true for everyone who is involved in the conversation;
  • Listen in a manner that communicates to the other person, “Help me understand your perspective/wants/needs ….”; and
  • Take the lead in problem-solving.

See Difficult Conversations, How to Discuss What Matters Most (originally published 1999).

In addition to explaining the difficult-conversations model, what else should a training program address?

Successfully managing difficult conversations requires an understanding of workplace and people dynamics. This makes it important to supplement difficult-conversations training with additional content.

You know that every person in your workplace brings a unique personality along with a series of psychological needs. Because it’s unlikely that any one person will change—we are who we are—it is critically important that legal professionals develop an awareness of specific actions that they may undertake that will facilitate or impede these conversations. I have found that training based upon the DISC behavioral style model and/or the StrengthsFinder assessment tool can be especially useful in helping lawyers understand how they may flex to the needs of others.

Please note, I discourage any law firm or law school from offering difficult-conversation training that does not include a good amount of interaction. Just as no one learns how to make an omelet simply by watching an on-line video, no one can become facile at conducting difficult conversations without practicing. I have found that program breaks for self-reflection, facilitated group exercises and individual coaching sessions are particularly useful.

What benefits will you accrue from providing difficult-conversations training?

PD professionals within the legal industry regularly tell new and established lawyers that they must take responsibility for their careers. Difficult-conversations training gives them a tool that helps them do just that. I encourage you to include such training in your firm’s new associates’ orientation programming.

PD professionals increasingly are asked to provide training that will help build resilience among lawyers and law students. Assertive communication skills are key component of many resiliency programs, including the initiative implemented by the U.S. Army and referenced in the 2017 Report of the National Task Force on Lawyer Well-Being. Difficult conversations training teaches this resiliency technique.

Law schools that incorporate this training into their curriculum achieve the goal of developing lawyers who are better prepared to meet the needs of those who consume legal services. Difficult conversations lie at the heart of any dispute resolution effort.

What additional resources should you explore?

The following books are worth your time and attention:

Crucial Conversations Tools for Talking When Stakes Are High, by K. Patterson, J. Grenny, R. McMillan, and A. Switzler

Fierce Conversations: Achieving Success at Work and in Life One Conversation at a Time, by S. Scott

Getting Past No: Negotiating in Difficult Situations, by W. Ury

Getting to Yes: Negotiating Agreement Without Giving In, by R. Fisher, W. Ury, and B. Patton

You will also find a plethora of articles on difficult conversations on the Harvard Business Review website ( 



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